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Pittsfield, MA accommodations
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288 Lodgings in Pittsfield, MA

Search Lodgings near the Old Town in Pittsfield, MA

Choosing central accommodation in downtown Pittsfield, MA maximizes your time, putting popular museums, historic districts, and local restaurants within walking distance.

Solomon Ely Homestead - Charming Pittsfield Stay - Pittsfield, MA
10 2 reviews

Solomon Ely Homestead - Charming Pittsfield Stay

apartment, Pittsfield
This Pittsfield vacation home offers a central location, within a 10-minute walk of the Berkshire Athenaeum, Colonial Theatre, and Berkshire Museum, and less than a mile from the Barrington Stage Company and the Housatonic River.
This four-bedroom, two-bathroom house sleeps seven and features a fully equipped kitchen with a refrigerator, microwave, dishwasher, and a coffee/tea maker, plus a Smart TV, in-unit laundry, and on-site parking.
Spacious 2 Bedroom Downtown Very Nice Area! - Pittsfield, MA
9.6 49 reviews

Spacious 2 Bedroom Downtown Very Nice Area!

apartment, Pittsfield
This Pittsfield apartment rental is centrally located, a 5-minute walk from downtown's main street, offering easy access to numerous cafes, restaurants, shops, and a movie theater.
The two-bedroom, one-bathroom unit comfortably sleeps four guests and includes amenities such as air conditioning, internet, and parking.
Downtown Apartment A - Pittsfield, MA
9.9 107 reviews

Downtown Apartment A

apartment, Pittsfield
This Pittsfield apartment is conveniently located in a quiet neighborhood, just 5 minutes from Bousquet Ski Area and close to Jimmy Peak, making it ideal for winter sports enthusiasts. The apartment has received excellent ratings for user experience, location, and cleanliness.
The apartment is a 2-bedroom rental that can accommodate up to 4 guests. It features a full kitchen with a fridge, freezer, and microwave oven, along with air conditioning, parking, and internet access. The apartment is close to Tanglewood, Mass MoCA, hiking trails, and a variety of restaurants, offering easy access to cultural and outdoor activities.
Hawksnest: Quiet 2br Apt, Heart Of The Berkshires - Pittsfield, MA
9.7 194 reviews

Hawksnest: Quiet 2br Apt, Heart Of The Berkshires

apartment, Pittsfield
This renovated Pittsfield apartment, conveniently located off Highway 7, provides easy access to Berkshire attractions like Kripalu Center for Yoga & Health, Lenox, and Tanglewood (all within 15 minutes).
The 2-bedroom, 1-bathroom rental offers a private entrance, a screened porch, shared backyard access, and accommodates up to 4 guests with amenities including air conditioning, free internet, and parking.

Choose the Right Family Lodgings in Pittsfield, MA

These family-friendly lodgings in Pittsfield, MA offer plenty of room and keep city attractions within easy reach; find the perfect fit for your group.

Cantabile Life In The Berkshires - Pittsfield, MA
9.9 217 reviews

Cantabile Life In The Berkshires

apartment, Pittsfield
This apartment is located in a quiet, friendly neighborhood in Pittsfield, just minutes from several lakes, mountains, and attractions like Tanglewood and Bousquet Ski Area. It boasts excellent ratings for location, cleanliness, and user satisfaction.
The rental offers three bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy the spacious living areas, well-equipped kitchen, and outdoor space, plus family-friendly amenities like games, a piano, and child-friendly equipment.
Lake Views & Dock Access - Pittsfield Cottage! - Pittsfield, MA
10 5 reviews

Lake Views & Dock Access - Pittsfield Cottage!

cottage, Lanesborough
This Lanesborough lakeside home is located near Pontoosuc Lake, just two miles from Balanced Rock State Park, five miles from Pittsfield State Forest, and eight miles from Jiminy Peak Mountain Resort. This five-bedroom, two-bathroom vacation rental boasts 2,000 square feet of space, sleeps up to eight guests, includes a private boat dock, kayaks, canoes, and a pedal boat, and offers amenities such as WiFi, central air conditioning, and a gas grill.
Berkshire Lakehouse - 3 Bedrooms - Sleeps 5 - Pittsfield, MA
9.8 49 reviews

Berkshire Lakehouse - 3 Bedrooms - Sleeps 5

apartment, Pittsfield
This Pittsfield lake house, situated on Onota Lake with private dock access and proximity to Pittsfield's ski slopes and hiking trails, offers a perfect base for exploring the Berkshires. This three-bedroom, one-bathroom home sleeps five, features a fully equipped kitchen, laundry facilities, a large deck, fenced yard, and access to kayaks and paddleboards.
Marie's Place - Pittsfield, MA
9.8 318 reviews

Marie's Place

apartment, Pittsfield
This apartment is located in Pittsfield, just a short drive from the city's cultural attractions like the Berkshire Museum, Colonial Theater, and Barrington Stage Company. It has excellent user, location, and cleanliness ratings, making it a great choice for travelers. The apartment is fully furnished and comfortably accommodates up to four guests. You'll enjoy convenient on-site laundry facilities, off-street parking, and access to the yard and parking area, making your stay hassle-free.

Frequently Asked Questions about accommodations in Pittsfield, MA

  • What are the top attractions and must-see sites in Pittsfield, MA?

    You definitely want to check out the Berkshire Museum, it has a great collection of art and history. The Clark Art Institute is also a must-see, they have an amazing collection of Impressionist and early modern art, and the grounds are beautiful. And don't forget about the Barrington Stage Company, they put on some great shows throughout the year.
  • What are the best accommodations in Pittsfield, MA?

    Among the accommodations in Pittsfield, MA, Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield are the most popular ones.

  • Which cultural festivals and seasonal events should visitors attend in Pittsfield, MA?

    The biggest event is the 10 Days of Summer festival in July, it's a great way to experience local music and art. You should also check out the Pittsfield Farmers Market on Saturdays, it's a great place to get fresh produce and local crafts. And if you're in town during the fall, you can't miss the foliage, it's absolutely stunning.
  • What are the best accommodations with a pool in Pittsfield, MA?

  • What are the most convenient modes of transportation within Pittsfield, MA?

    Pittsfield is pretty walkable, especially downtown. You can also take the bus, the Berkshire Regional Transit Authority has routes throughout the city. If you're planning on exploring the surrounding area, renting a car is your best bet.
  • What are the best accommodations with a jacuzzi in Pittsfield, MA?

  • What outdoor activities and adventures are popular in and around Pittsfield, MA?

    There's plenty to do outdoors in Pittsfield. You can hike or bike the Appalachian Trail, go kayaking on Lake Onota, or visit the nearby Mount Greylock State Reservation, the highest point in Massachusetts. You can also check out the Taconic Crest Trail, which runs along the Taconic Mountains.
  • What are the best accommodations for families and kids in Pittsfield, MA?

    The best accommodations for families and kids in Pittsfield, MA are Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield.

  • What types of accommodations are available in Pittsfield, MA?

    You can find everything from budget-friendly motels to upscale hotels in Pittsfield. There are also a few bed and breakfasts and vacation rentals available. You can also find some great places to stay in the nearby towns of Lenox and Stockbridge.
  • What are the best pet friendly accommodations in Pittsfield, MA?

    The best pet friendly accommodations in Pittsfield, MA are Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield.

  • When is the best time to visit Pittsfield, MA?

    The best time to visit Pittsfield is in the fall, when the leaves change color. It's also a great time to visit in the summer, when the weather is warm and there are lots of outdoor activities to enjoy. You can find some great deals on accommodations during the shoulder seasons, too.
  • What are the best accommodations with parking in Pittsfield, MA?

    Hotel On North, Best Western Plus Berkshire Hills Inn & Suites and Hilton Garden Inn Lenox Pittsfield are the best accommodations with parking in Pittsfield, MA.

  • What local dishes and culinary experiences are a must-try in Pittsfield, MA?

    You have to try the Berkshire pork. It's a local specialty, and there are plenty of restaurants in Pittsfield that serve it. You should also check out the local breweries, they're making some really great craft beers. You can also find some great Italian food in Pittsfield, it's a popular cuisine here.
  • In which part of Pittsfield, MA should you consider renting accommodation?

    Downtown Pittsfield is a good choice, it's close to all the action and has a good selection of restaurants and shops. If you're looking for something quieter, you might want to consider staying in the nearby town of Lenox, which is known for its beautiful scenery and charming shops.

Popular destinations

Best Pittsfield, MA accommodation with a kitchen

Cozy Bungalow In Se Pittsfield - Pittsfield, MA
9.9 30 reviews

Cozy Bungalow In Se Pittsfield

apartment, Pittsfield
This Pittsfield apartment is located just 5 minutes from Bousquet Ski Mountain and 20 minutes from Jiminy Peak, offering easy access to outdoor activities in the Berkshires. The apartment has received excellent ratings for location, cleanliness, and overall user experience.
The rental is a single-floor home with space for 5 guests. It features a fully equipped kitchen, a private garden, a deck and an enclosed porch, and a grill for cookouts, making it ideal for entertaining friends and family.
Spacious Historic Home In The Berkshires! - Pittsfield, MA
9.0 1 review

Spacious Historic Home In The Berkshires!

house, Pittsfield
This five-bedroom Pittsfield vacation home is conveniently located 7.6 miles from Tanglewood and 7.8 miles from the Cranwell Spa & Golf Club, offering easy access to area attractions.
The 3,300-square-foot property boasts a fully equipped kitchen, in-house laundry, a fireplace, and accommodates up to 17 guests, perfect for large families or groups visiting the Berkshires.
Centrally Located In The Berkshires - Cozy Bungalow In Se Pittsfield! - Pittsfield, MA
10 5 reviews

Centrally Located In The Berkshires - Cozy Bungalow In Se Pittsfield!

apartment, Pittsfield
This centrally located bungalow in Pittsfield is just minutes away from popular attractions such as Bousquet Ski Resort, hiking trails, museums, and Tanglewood in Lenox. It offers easy access to urban amenities, and has been rated as "excellent" by previous guests.
The bungalow has a floor area of 1000 square feet and can accommodate up to 5 guests. It has 2 bedrooms, 1 bathroom, a kitchen with a fridge, microwave oven, and dishwasher, and air conditioning. The bungalow also features a spa, an outdoor deck, a yard with games and a grill, and convenient access to hiking trails and museums.
Renovated Pittsfield Colonial By Evergreen Home - Pittsfield, MA
9.9 101 reviews

Renovated Pittsfield Colonial By Evergreen Home

apartment, Pittsfield
This Pittsfield apartment is in the heart of the Berkshires, surrounded by museums, theaters, and hiking trails. It has excellent user, location, and cleanliness ratings.
The apartment has 4 bedrooms, 3 bathrooms, and a bonus room, with a floor area of 3900 square feet. It can accommodate up to 12 guests. The kitchen has new appliances, and there's a large deck overlooking a private backyard and woods. Other amenities include Wi-Fi, a washer and dryer, a fitness center, and parking.

Neighborhoods and points of interest in Pittsfield, MA

Best Pittsfield, MA accommodation with parking

Dancing Horse Lodge - Pittsfield, MA
9.7 369 reviews

Dancing Horse Lodge

apartment, Pittsfield
This vacation rental is located in the mountains, just a short drive from Pittsfield's cultural attractions like the Colonial Theater, Berkshire Museum, and Housatonic River. The house has earned excellent ratings for its cleanliness, location, and overall experience.
The home has 3 bedrooms and 1 bathroom, comfortably accommodating up to 6 guests. Enjoy amenities like a fully equipped kitchen, a garden, and a relaxing mountain setting.
Beautiful Lake-view Getaway! - Pittsfield, MA
9.9 67 reviews

Beautiful Lake-view Getaway!

apartment, Pittsfield
This Pittsfield lakeside rental boasts stunning lake views and easy access to Berkshire attractions, offering a perfect base for exploring the region.
This two-bedroom, one-bathroom house sleeps four, features a full kitchen with dishwasher, a jacuzzi, a fire pit, and a patio—ideal for year-round getaways, from summer lake recreation to winter skiing.
Spacious Green 2 Bedroom Downtown - Pittsfield, MA
9.6 51 reviews

Spacious Green 2 Bedroom Downtown

apartment, Pittsfield
This Pittsfield apartment rental is conveniently located a 5-minute walk from numerous restaurants and a movie theater in downtown Pittsfield.
The two-bedroom, one-bathroom unit sleeps five and includes a full kitchen with fridge, microwave, and dishwasher, in-unit laundry, air conditioning, and off-street parking.

Best Pittsfield, MA lodging with a pool

Among the 288 accommodations in Pittsfield, MA, here are the 1 best ones with a pool

Lenox Grand Colonial With Pool By Evergreen Home - Pittsfield, MA
10 3 reviews

Lenox Grand Colonial With Pool By Evergreen Home

apartment, Lenox

Browse 5-Star Accommodations in Pittsfield, MA

Comfort and a prime location define these luxury lodgings in Pittsfield, MA, each hand-selected with your total relaxation in mind.

Dancing Horse Lodge - Pittsfield, MA
9.7 369 reviews

Dancing Horse Lodge

apartment, Pittsfield

Top-Rated Pet-Friendly Lodgings in Pittsfield, MA

Traveling with a pet to Pittsfield, MA is effortless when your lodging is equipped with nearby dog parks and city walks right on the doorstep.

Wildlife Lakeside Cottage;  Views/wildlife - Pittsfield, MA
9.7 373 reviews

Wildlife Lakeside Cottage; Views/wildlife

apartment, Lanesborough
Net Zero Home With Rustic Berkshire Charm - Pittsfield, MA
9.9 133 reviews

Net Zero Home With Rustic Berkshire Charm

apartment, Pittsfield
3 Acres, Mtn Views, Hot Tub, Steps To Winery - Pittsfield, MA
No reviews

3 Acres, Mtn Views, Hot Tub, Steps To Winery

apartment, Richmond
13-min Jiminy, Fave, Hot Tub, Lg Open Lr, Family - Pittsfield, MA
No reviews

13-min Jiminy, Fave, Hot Tub, Lg Open Lr, Family

house, Lanesborough
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